WO2002074830A1 - Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof - Google Patents

Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof Download PDF

Info

Publication number
WO2002074830A1
WO2002074830A1 PCT/US2002/007301 US0207301W WO02074830A1 WO 2002074830 A1 WO2002074830 A1 WO 2002074830A1 US 0207301 W US0207301 W US 0207301W WO 02074830 A1 WO02074830 A1 WO 02074830A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
polyurethane
geotextile
isocyanate
composite
Prior art date
Application number
PCT/US2002/007301
Other languages
English (en)
French (fr)
Inventor
Peter H. Markusch
Ashok M. Sarpeshkar
Marylyn Donaldson
Iii Tracy W. Estabrook
Ralf Guether
Original Assignee
Bayer Polymers Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Polymers Llc filed Critical Bayer Polymers Llc
Priority to MXPA03008233A priority Critical patent/MXPA03008233A/es
Priority to EP02719191A priority patent/EP1381638A1/en
Priority to PL02364136A priority patent/PL364136A1/xx
Priority to CA002440881A priority patent/CA2440881A1/en
Publication of WO2002074830A1 publication Critical patent/WO2002074830A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates to a polyurethane geotextile composite having improved water resistance. Additionally, the present invention relates to a process for forming a polyurethane geotextile composite having improved water resistance.
  • Losses in the distribution of water using unlined irrigation ditches are estimated at a minimum to be 25% and in some situations to be more than 50% depending upon the porosity of the ditch surface and the distance the water is being moved.
  • ditches are formed by excavating the soil to the desired depth and width. The water moves through the ditch in contact with the exposed natural surface. This can be sand, clay, rocks, etc. and, more commonly, mixtures thereof. The porosity will depend upon the proportions of the different components in the soil.
  • the loss of water in unlined irrigation ditches at one time was considered acceptable only because the supply of water exceeded demand. However, as civilization has developed and world population has increased, more water is required for both greater food production and for the marked by increasing in non-agriculture uses.
  • the liquid polyurethane soaked geotextile composite is then placed over the surface of an area to be lined and allowed to cure, to form a polyurethane/geotextile composite.
  • One drawback of the mixture taught by the ' 677 patent is that the filler in the mixture is often not completely dry and can absorb additional moisture from the atmosphere. Moisture is always present when the mixture is applied under relatively humid conditions. This water will react with the polyisocyanate and cause the mixture to foam. Foaming weakens the strength and impermeability of the composite.
  • the polyurethane geotextile composite when stored under water (such as in a ditch or canal liner application), can absorb considerable amounts of water (i.e., 1-2%) which swells and weakens the liner.
  • water i.e., 1-2%
  • the present invention relates to a polyurethane geotextile composite with improved water resistance useful as a liner for a ditch or canal in which the polyurethane used is a reaction product of a mixture comprising: a) a liquid polyisocyanate havjng an ispcyanate content of at least 10% by weight, b) an isocyanate-reactive component comprising:
  • the invention further relates to a process for producing a polyurethane geotextile composite liner with improved water resistance in which a geotextile is impregnated with such polyurethane.
  • the invention is also directed to a ditch or canal lined with such polyurethane geotextile composite and to a process for lining a ditch or canal with such composite.
  • the advantage of the polyurethane composition used to produce the composite of the present invention is that it has less tendency to foam.
  • the geotextile polyurethane composite of the present invention will, therefore, be characterized by low water absorption. When such composite is used to line a ditch and/or a canal, water loss is kept at a minimum.
  • the present invention relates to a polyurethane geotextile composite which is suitable for use as a liner with improved water resistance which is produced by impregnating a geotextile with a polyurethane composition that is a reaction product of a mixture which includes: a) a liquid polyisocyanate having an isocyanate content of at least 10% by weight, b) an isocyanate-reactive component which includes:
  • the invention is also directed to a method for making such composites, ditches and canals lined with such composites and to a method for lining ditches and canals with such composites.
  • a ditch or canal is lined with the polyurethane geotextile composite of the present invention by dispensing a polyurethane composition having improved water resistance onto a geotextile or otherwise impregnating the geotextile with the polyurethane composition, laying the polyurethane-impregnated geotextile onto a surface of a ditch or canal before the polyurethane has fully cured, conforming the polyurethane impregnated geotextile to the shape of the surface of the ditch or canal, and allowing the polyurethane to fully cure to form a polyurethane geotextile composite liner.
  • the polyurethane composition having improved water resistance is a reaction product of the above described components a), b) and c).
  • the polyurethane composition having improved water resistance may be applied onto one or more geotextiles.
  • a second polyurethane Mo-5940 7 impregnated geotextile may be laid on the surface of a canal or ditch which has previously been lined with the liquid polyurethane composition is fully cured, if desired. Subsequently the polyurethane- impregnated geotextile is conformed to the shape of the surface of the canal or ditch where the polyurethane geotextile composite is allowed to fully cure.
  • the polyurethane composition having improved water resistance used in this process is less likely to foam under humid conditions and produces a composite with less water absorption.
  • the term "geotextile” refers to any woven or non- woven porous blanket or mat which is produced from natural or synthetic fibers. Also, as used herein, the terms “ditch” and “canal” are used interchangeably and can refer to any liquid carrying surface having a depression or grade.
  • Geotextiles are used primarily to line earthen surfaces. Such liners may, however, also be used to line roofs, ponds, reservoirs, landfills, underground storage tanks, canals and ditches. Examples of geotextiles include woven or non-woven polypropylene, polyester, jute, cotton and fiberglass fabrics. Any of the known goetextiles may be used in the practice of the present invention. Any of the known liquid isocyanates having an isocyanate content of at least 10% by weight, preferably at least 20% by weight, most preferably at least 30% by weight, which are liquid under the processing conditions used may be used in the practice of the present invention.
  • Suitable liquid organic polyisocyanates include aliphatic, cycloaliphatic, araliphatic, aromatic, and heterocyclic polyisocyanates of the type described, for example, by W. Siefken in Justus Liebigs Annalen der Chemie, 562, pages 75 to 136.
  • Such isocyanates include those represented by the formula Q(NCO) n in which n represents a number from 2 to about 5, preferably 2 to 3, and Q represents an aliphatic hydrocarbon group containing from 2 to about 18, preferably 6 to 10, carbon atoms, a cycloaliphatic hydrocarbon group containing from 4 to about 15, preferably Mo-5940 from 5 to 10, carbon atoms, an araliphatic hydrocarbon group containing from 8 to 15, preferably from 8 to 13, carbon atoms, or an aromatic hydrocarbon group containing from 6 to about 15, preferably 6 to 13, carbon atoms.
  • Suitable isocyanates include: ethylene diisocyanate; 1 ,4-tetramethylene diisocyanate; 1 ,6-hexamethylene diisocyanate; 1 ,12-dodecane diisocyanate; cyclobutane- 1 ,3-diisocyanate; cyclohexane-1 ,3- and 1 ,4- diisocyanate, and mixtures of these isomers; 1- isocyanato- 3,3,5- trimethyl-isocyanatomethylcyclohexane ("isophorone diisocyanate" (See, e.g. German Offenlegungsschrift 1 ,202,785 and U.S. Patent No.
  • Pat. No. 3,492,330 m- and p-isocyanatophenyl sulfonylisocyanates (of the type described in U.S. Patent No. 3,454,606); perchlorinated aryl polyisocyanates (of the type described, for example, in U.S. Patent No. 3,227,138); modified polyisocyanates containing carbodiimide groups (of the type described in U.S. Patent No. 3,152,162); modified polyisocyanates containing urethane groups (of the type described, for example, in U.S. Patent Nos.
  • modified polyisocyanates containing allophanate groups (of the type described, for example, in British Patent 994,890, Belgian Patent 761 ,616, and published Dutch Patent Application 7,102,524); modified polyisocyanates containing isocyanurate groups (of the type described, for example, in U.S. Patent No.
  • polyisocyanates such as 2,4- and 2,6-toluene diisocyanates and their isomer mixtures ("TDI”); diphenyl methane diisocyanate (“MDI”); polymethylene poly(phenylisocyanates) of the type obtained by condensing aniline with formaldehyde, followed by phosgenation ("crude MDI”); and polyisocyanates containing carbodiimide groups, urethane groups, allophanate groups, isocyanurate groups, urea groups, or biuret groups ("modified polyisocyanates").
  • TDI 2,4- and 2,6-toluene diisocyanates and their isomer mixtures
  • MDI diphenyl methane diisocyanate
  • CAde MDI polymethylene poly(phenylisocyanates) of the type obtained by condensing aniline with formaldehyde, followed by phosgenation
  • the isocyanate-reactive component used to produce the polyurethane composition includes either (1) a combination or blend of castor oil or a modified castor oil and a polyether polyol, or (2) a modified castor oil which is a reaction product of castor oil or a modified castor oil with a polyether polyol.
  • suitable isocyanate- reactive components include: (i) from about 20 to 90% by weight, preferably 40 to 80% by weight, based on total weight of the isocyanate- reactive component, of castor oil having an OH number of from 160 to 170, a viscosity of from 500 to 900 mPa-s at 25°C, and a water content of less than 0.5% by weight, based on the total weight of castor oil, and (ii) from about 10 to 80% by weight, preferably 20 to 60% by weight, based on total weight of isocyanate-reactive component, of a polyether polyol having an OH number of from 28 to 700, preferably from 112 to 500, a functionality of from 3 to 8, preferably from 4 to 7, most preferably 2 to 3, a number average molecular weight of from about 240 to about 6,000, preferably from about 400 to about 4,000, most preferably from about 400 to about 2,000, and a viscosity of from 50 to 3
  • polyether polyols prepared from alkylene oxides in which at least 70% by weight, preferably at least 90% by weight, of the alkylene oxide content is propylene oxide are particularly suitable for the present invention. It is also advantageous to use an isocyanate-reactive component containing less than 0.5% by weight, preferably less than 0.1% by weight, based on total weight of isocyanate-reactive component of water.
  • Suitable polyether polyols useful in component b) include polyethers prepared, for example, by the polymerization of epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide, or epichlorohydrin, optionally in the presence of Lewis acids such as BF 3 , or prepared by chemical addition of such epoxides, optionally added as mixtures or in sequence, to starting components containing reactive hydrogen atoms, such as water, alcohols, or amines.
  • epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide, or epichlorohydrin
  • Lewis acids such as BF 3
  • epoxides optionally added as mixtures or in sequence, to starting components containing reactive hydrogen atoms, such as water, alcohols, or amines.
  • starting components include: ethylene glycol, 1 ,3- or 1 ,2-propanediol, 1 ,2-, 1 ,3-, or 1 ,4-butanediol, trimethylolpropane, 4,4'-dihydroxydiphenylpropane, aniline, ammonia, ethanolamine, and ethylene diamine.
  • Offenlegungsschriften 1 ,176,358 and 1,064,938 may also be used.
  • Polyethers which contain predominantly primary hydroxyl groups (up to about 90% by weight, based on all of the hydroxyl groups in the polyether) are also suitable.
  • Polyethers modified by vinyl polymers of the kind obtained, for example, by the polymerization of styrene and acrylonitrile in the presence of polyethers are also suitable, as are polybutadienes containing hydroxyl groups.
  • polyether polyols include polyoxyalkylene polyether polyols, such as polyoxypropylene diol, polyoxybutylene diol, and polytetramethylene diol, as well as polyoxypropylene polyoxyethylene triols.
  • PHD polyols include the so-called "PHD polyols", which are prepared by reaction of an organic polyisocyanate, hydrazine, and a polyether polyol.
  • PHD polyols prepared by reaction of an organic polyisocyanate, hydrazine, and a polyether polyol.
  • U.S. Patent No. 3,325,421 discloses a method for producing suitable PHD polyols by reacting a stoichiometric or substoichiometric quantity (relative to diamine) of polyisocyanate dissolved in a polyol having a molecular weight of at least 500 and a hydroxyl number of no more than 225. See also U.S. Patent Nos. 4,042,537 and 4,089,835.
  • polyether polyols useful in the present invention include the so-called "polymer polyols", which are prepared by polymerizing styrene and acrylonitrile in the presence of a polyether. See, for example, U.S. Patent Nos. 3,383,351 , 3,304,273, 3,523,093, 3,652,639, 3,823,201 and 4,390,645.
  • the most preferred polyethers are polyoxypropylene polyethers that do not contain ethylene oxide.
  • any of the known low molecular weight organic diols or triols may optionally be included in the isocyanate-reactive component b) of the present invention in an amount of up to 10% by weight, based on total weight of component b).
  • Suitable organic diols and triols have equivalent weights of from about 31 to 99. Examples of such diols and triols include: Mo-5940 12
  • 2-methyl-1 ,3-propranediol ethylene glycol; 1 ,2- and 1 ,3-propanediol; 1 ,3-, 1 ,4- and 2,3-butanediol; 1 ,6-hexanediol; 1 ,10-decanediol; diethylene glycol; triethylene glycol; tetraethylene glycol; dipropylene glycol; tripropylene glycol; glycerol; trimethylolpropane; neopentyl glycol; cyclohexanedimethanol; and 2,3,4-trimethylpentane-1 ,3-diol.
  • Preferred diols and triols include dipropylene glycol and tripropylene glycol.
  • the reaction mixture from which the polyurethanes used in the present invention are produced also contains a catalyst c) for catalyzing the reaction between isocyanate groups and hydroxyl groups (i.e., a urethane catalyst).
  • a catalyst c) for catalyzing the reaction between isocyanate groups and hydroxyl groups i.e., a urethane catalyst.
  • Such catalysts are well known in the art and are generally used in an amount which is no greater than 0.5 parts by weight per 100 parts by weight of isocyanate-reactive component, preferably from 0.0001 to 5 parts by weight, most preferably from 0.0001 to 0.1 parts by weight.
  • Suitable catalysts include the organometallic catalysts.
  • Preferred catalysts c) are organic tin compounds.
  • the organic tin compounds are preferably tin(ll) salts of a carboxylic acid such as tin(ll) acetate, tin(ll) octoate, tin (II) ethyl hexoate and tin (II) laurate and tin (IV) compounds such as dibutyl tin oxide, dibutyl tin dichloride, dibutyl tin diacetate, dibutyl tin dilaurate, dibutyl tin maleate, dioctyl tin diacetate and the like.
  • urethane catalysts which are well known to those skilled in the art of polyurethane chemistry. It is preferred to use organometallic compounds.
  • the catalyst can be added separately to the polyurethane-forming reaction mixture or it may be combined with the isocyanate-reactive component prior to combining the polyisocyanate and polyol components.
  • Catalysts which catalyze the reaction of isocyanate groups with water should not be included in the polyurethane- forming reaction mixture.
  • fillers can be used in the present invention.
  • the fillers useful herein are also known.
  • Useful fillers include calcium carbonate, barium sulfate, kieselguhr, whiting, mica, glass fibers, liquid crystal fibers, Mo-5940 glass flakes, glass balls, aramide fibers, and carbon fibers.
  • ground solid plastics such as polyurethane scrap
  • rubber wastes such as from tires
  • any kind of ground rubber may be used.
  • fillers are used, they can be added to either the polyisocyanate or the isocyanate-reactive component prior to forming the polyurethane- forming reaction mixture or they may be separately metered into the mixture.
  • liquid polyisocyanate component a) is mixed with isocyanate reactive component b) in the presence of a urethane catalyst c) at an NCO : OH equivalent ratio of from 1.4 : 1 to 0.9 : 1 , preferably from 1.1 :1.0 to 1.0 to 1.0.
  • the polyurethane geotextile composites having improved water resistance of the present invention can be formed as a liner for a ditch and/or canal.
  • the ditch and/or canal lining is made with a machine such as that described in United States Patent Number 5,639,331 ("the '331 patent").
  • the '331 patent teaches a mobile ditch lining apparatus having reservoirs for supplying raw materials such as resin, catalysts, fillers, colors or other additives.
  • the reservoirs are connected to a mixing chamber through flexible conduit means.
  • the delivery rate of the raw materials to the mixing chamber will vary depending upon the particular formulation and the quantity of the formulation required for a specific area of the liner being formed.
  • the components used to produce the polyurethane composition having improved water resistance are mixed in the mixing chamber.
  • the polyurethane composition having improved water resistance is applied to one or more geotextiles.
  • the geotextiles are pulled from a vat containing the polyurethane composition having improved water resistance through an adjustable die.
  • the opening of the die evenly distributes of the polyurethane on the geotextile(s), Mo-5940 14 determines how much polyurethane is dispensed on the geotextile(s), and also controls the thickness of the polyurethane-impregnated geotextile composite.
  • the polyurethane-impregnated geotextile is then cut to the desired length and placed in the canal or ditch where it conforms to the surface and cures to form a polyurethane geotextile composite liner.
  • the polyurethane composition having improved water resistance is applied to the geotextile by spraying using commercially available two-component polyurethane spray equipment.
  • the polyurethane-impregnated geotextile is subsequently placed in the ditch or canal where it conforms to the surface and cures to form a polyurethane geotextile composite.
  • the geotextile can also first be cut to size, placed in the canal or ditch and subsequently sprayed with the polyurethane composition having improved water resistance.
  • the geotextile with the still liquid polyurethane on it is rolled with a paint roller to allow the polyurethane to penetrate through the geotextile and onto the surface of the ditch or canal.
  • the polyurethane composition having improved water resistance is first sprayed on any cracked or broken concrete of a concrete lined ditch or canal and subsequently a geotextile is placed over the polyurethane-coated concrete in a manner such that the geotextile absorbs the still liquid polyurethane to form a polyurethane-impregnated composite which subsequently cures to form a solid yet flexible polyurethane geotextile composite.
  • any of the above processes can be repeated one or more times.
  • the thickness of the polyurethane geotextile composite can be varied over a wide range but usually measures from about 50 microns to about 500 microns.
  • the amount of polyurethane applied to the geqtextile(s) can be varied but usually the amount of polyurethane applied per square meter of geotextile ranges from 1 kg to 20 kg, preferably from 2 kg to 5 kg. If desirable several layers of the polyurethane-impregnated geotextile(s) may be applied over each other to obtain a composite of higher strength and dimensional stability. Such multi-layered composite(s) are actually preferred for lining an earthen canal or ditch.
  • Isocyanate A polymethylene poly (phenylisocyanate) having an NCO content of about 31.5%, a functionality of 2.6 and a viscosity at 25°C of 200 mPa-s.
  • Polyol 1 a monoethanolamine-started propylene oxide polyether polyol, having an OH number of about 350, a functionality of about 3 and a number average molecular weight of about 480.
  • Mo-5940 a monoethanolamine-started propylene oxide polyether polyol, having an OH number of about 350, a functionality of about 3 and a number average molecular weight of about 480.
  • Polyol 2 a glycerine-started propylene oxide polyether polyol, having an OH number of about 250, a functionality of about 3 and a number average molecular weight of about 670.
  • Polyol 3 a propylene glycol-started propylene oxide polyether polyol, having an OH number of 56, a functionality of about 2 and a number average molecular weight of about 2000.
  • Polyol 4 a propylene glycol-started propylene oxide polyether polyol, having an OH number of 264, a functionality of about 2 and a molecular weight of about 425.
  • Polyol 5 Castor Oil, DB, (CasChem, Inc.) (water content ⁇ 0.5%).
  • Catalyst A dimethyltin dilaurate, commercially available as Fomrez UL-28 from Witco.
  • Geotextile A Typar-3301 , spunbonded polypropylene, 3oz/yd 2 , 12 mils thickness (Reemay)
  • Geotextile B FX-40HS, polypropylene, nonwoven, heatbonded, 4oz/yd 2 (Carthage Mills)
  • Geotextile C Trevira Spunbound Type 1620, polyester, nonwoven, heatbonded, 5.7oz yd 2 , 37 mils thickness, (Fluid Systems) The following polyol blends were used in these Examples:
  • Polyol Blend A 10 pbw Polyol 1 45 pbw Polyol 2 45 pbw Polyol 3 0.01 pbw Catalyst A Mo-5940 17
  • Polyol Blend B 80 pbw Polyol 5
  • the polyol blend indicated in Table 1 and Isocyanate A were hand mixed in the amounts indicated in Table 1 at 25-30°C for about 2 minutes, and then poured into a book-case mold which measured 8 in. x 16 in. x 0.125 in. at room temperature.
  • the cast samples were allowed to cure at room temperature for 16 hours before demolding.
  • the samples were stored for at least 1 week at room temperature in a temperature and humidity controlled environment and then tested for various physical and mechanical properties. The results of these tests are reported are in Table 1.
  • Example 2 The polyurethane prepared from Polyol Blend B and Isocyanate A (Example 2) in accordance with the present invention showed superior physical properties and significantly lower water absorption than the polyurethane prepared with Polyol Blend A in which no Castor Oil was present (Comparative Example 1).
  • Examples 3-5 Comparative
  • Polyurethane geotextile composites were prepared according to the following procedure: 100 g of Polyol Blend A, and 42.6 g of Isocyanate A were mixed and then poured onto a 1 sq. ft. piece of geotextile A. The polyurethane- forming reaction mixture was spread out with a spatula and one sq. ft. of a second Geotextile (A, B or C) was placed on top of the liquid polyurethane. A rubber roller was then rolled over the second geotextile to evenly distribute the polyurethane mixture between the geotextiles and also to roll off any excess of polyurethane. The material cured to a solid geotextile polyurethane composite in about 1 hour.
  • the amount of resin in the composite was typically about 200 g/sq. ft. and the composite thickness ranged from 40 to 100 mils. All samples were prepared under high humidity conditions (>70%), and showed significant foaming before curing to form a solid polyurethane geotextile composite. The physical properties of each of these comparative composites were determined and the results are reported in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/US2002/007301 2001-03-15 2002-03-07 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof WO2002074830A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MXPA03008233A MXPA03008233A (es) 2001-03-15 2002-03-07 Revestimiento compuesto geotextil de poliuretano con mayor resistencia al agua y un procedimiento para su produccion.
EP02719191A EP1381638A1 (en) 2001-03-15 2002-03-07 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof
PL02364136A PL364136A1 (en) 2001-03-15 2002-03-07 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof
CA002440881A CA2440881A1 (en) 2001-03-15 2002-03-07 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/809,023 2001-03-15
US09/809,023 US6669407B2 (en) 2001-03-15 2001-03-15 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof

Publications (1)

Publication Number Publication Date
WO2002074830A1 true WO2002074830A1 (en) 2002-09-26

Family

ID=25200363

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/007301 WO2002074830A1 (en) 2001-03-15 2002-03-07 Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof

Country Status (8)

Country Link
US (1) US6669407B2 (es)
EP (1) EP1381638A1 (es)
CN (1) CN1240739C (es)
CA (1) CA2440881A1 (es)
MX (1) MXPA03008233A (es)
PL (1) PL364136A1 (es)
WO (1) WO2002074830A1 (es)
ZA (1) ZA200307149B (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7267288B2 (en) * 2001-03-22 2007-09-11 Nevada Supply Corporation Polyurethane in intimate contact with fibrous material
US20050058515A1 (en) * 2003-09-12 2005-03-17 Markusch Peter H. Geotextile/polymer composite liners based on waterborne resins
US7157010B1 (en) 2004-02-18 2007-01-02 Civil & Environmental Consultants, Inc. Polymeric flocculant infused silt fence
US8692030B1 (en) * 2006-04-20 2014-04-08 Pittsburg State University Biobased-petrochemical hybrid polyols
ATE466896T1 (de) * 2006-10-04 2010-05-15 Basf Se Vergussmassen auf basis von polyurethan
US8468968B2 (en) 2009-10-22 2013-06-25 Quest Inspar LLC Method and apparatus for lining pipes with isocyanate and hydroxyl-amine resin based on castrol or soy oil
CA2747460A1 (en) 2010-07-30 2012-01-30 Kent Weisenberg Method and apparatus for lining pipes with isocyanate and hydroxyl-amine resin based on castrol or soy oil
CN105671968B (zh) * 2014-05-20 2019-03-29 嘉兴富胜达染整有限公司 一种防护面料

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0130458A2 (de) * 1983-07-02 1985-01-09 Th. Goldschmidt AG Verwendung von Polyoxyalkylenethern des Rizinusöles zur Herstellung von Polyurethanen
US4582891A (en) * 1984-02-09 1986-04-15 Dai-Ichi Kogyo Seiyaku Co., Ltd. Process for inhibiting corrosion of polyurethane coating
US5421677A (en) * 1994-04-07 1995-06-06 Miles Inc. Process for forming a ditch liner

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2846814A1 (de) * 1978-10-27 1980-05-08 Bayer Ag Suspensionen von isocyanat-destillationsrueckstaenden in polyolen
DE2906091C3 (de) * 1979-02-17 1982-04-08 Fa. Carl Freudenberg, 6940 Weinheim Verwendung von Polyurethanen zur Heißversiegelung von textilen Flächengebilden
DE3015440A1 (de) * 1980-04-22 1981-10-29 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von polyurethan-kunststoffen unter verwendung von cyclischen, n-hydroxyalkyl-substituierten, amidingruppen aufweisenden verbindungen als katalysatoren
DE3227679A1 (de) * 1982-07-24 1984-02-02 Bayer Ag, 5090 Leverkusen Beschichteter verbundwerkstoff, verfahren zu seiner herstellung und seine verwendung zum auskleiden von durchlaessen
US4728710A (en) * 1986-11-28 1988-03-01 Ashland Oil, Inc. Sag resistant urethane adhesives with improved antifoaming property
US4743672A (en) * 1987-02-26 1988-05-10 Ashland Oil, Inc. Sag resistant, two component urethane adhesives
US4889915A (en) * 1987-04-14 1989-12-26 Caschem, Inc. Urethane adhesives
US4872784A (en) * 1988-08-23 1989-10-10 Le Roy Payne Ditch lining apparatus and method and product therefrom
US4955759A (en) 1988-08-23 1990-09-11 Le Roy Payne Ditch lining apparatus and method and product therefrom
US4955760A (en) 1988-08-23 1990-09-11 Le Roy Payne Laminate forming and applying apparatus and method and product therefrom
US5062740A (en) 1988-08-23 1991-11-05 Le Roy Payne Laminate forming and applying apparatus and method and product therefrom
US5166303A (en) * 1990-04-19 1992-11-24 Miles Inc. Expandable non-sagging polyurethane compositions
US5061776A (en) * 1990-11-19 1991-10-29 Hughes Aircraft Company Modified polyurethane flow-under thermal transfer adhesive
DE4134693A1 (de) * 1991-10-21 1993-04-22 Basf Ag Transparente, heissdampfsterilisierbare, nicht zytotoxische, im wesentlichen kompakte polyurethan-vergussmassen, verfahren zu ihrer herstellung und ihre verwendung, insbesondere fuer medizinisch-technische artikel
JPH09506641A (ja) * 1992-06-26 1997-06-30 ミネソタ マイニング アンド マニュファクチャリング カンパニー ポリウレタン／ポリ尿素エラストマー
US5378733A (en) * 1993-04-09 1995-01-03 Seaward International, Inc. Sound attenuating polymer composites
CA2159263A1 (en) * 1994-11-14 1996-05-15 Peter H. Markusch Non-sagging, sandable polyurethane compositions
DE4443432A1 (de) * 1994-12-06 1996-06-13 Elastogran Gmbh Unter Druck stehende, Treibmittel enthaltende Isocyanat-Semirpräpolymermischungen auf Basis von Mischungen aus Polyhydroxylverbindungen und Monoalkoholen und/oder Hydroxyketonen, ihre Verwendung zur Herstellung von Polyurethanschaumstoffen und ein Verfahren hierfür
KR100414602B1 (ko) * 1995-01-13 2004-02-18 에섹스 스페시얼티 프로덕츠, 인코오포레이티드 2-부분습윤경화성폴리우레탄접착제
US5770673A (en) * 1996-04-10 1998-06-23 Bayer Corporation Non-sagging, light stable polyurethane compositions, a process for producing them, and their use as seam sealants
WO1998008884A1 (en) * 1996-08-26 1998-03-05 Tyndale Plains-Hunter, Ltd. Hydrophilic and hydrophobic polyether polyurethanes and uses therefor
US6384130B1 (en) * 1999-12-03 2002-05-07 Bayer Corporation Liquid, hydrophobic, non-migrating, non-functional polyurethane plasticizers
US6248856B1 (en) * 1999-12-10 2001-06-19 Bayer Corporation One-shot polyurethane elastomers with very low compression sets
US6277943B1 (en) * 1999-12-10 2001-08-21 Bayer Corporation One-shot polyurethane elastomers with very low compression set
US6503980B2 (en) * 2000-12-20 2003-01-07 Bayer Corporation Liquid polyurethane plasticizers containing allophanate and/or carbodiimide and/or uretonimine groups

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0130458A2 (de) * 1983-07-02 1985-01-09 Th. Goldschmidt AG Verwendung von Polyoxyalkylenethern des Rizinusöles zur Herstellung von Polyurethanen
US4582891A (en) * 1984-02-09 1986-04-15 Dai-Ichi Kogyo Seiyaku Co., Ltd. Process for inhibiting corrosion of polyurethane coating
US5421677A (en) * 1994-04-07 1995-06-06 Miles Inc. Process for forming a ditch liner

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WEB-SITE, XP002203794, Retrieved from the Internet <URL:http://www.china-castoroil.com/html/eno1.htm> [retrieved on 20020627] *

Also Published As

Publication number Publication date
CN1496380A (zh) 2004-05-12
EP1381638A1 (en) 2004-01-21
CA2440881A1 (en) 2002-09-26
CN1240739C (zh) 2006-02-08
MXPA03008233A (es) 2005-03-07
US20020172565A1 (en) 2002-11-21
ZA200307149B (en) 2004-09-13
US6669407B2 (en) 2003-12-30
PL364136A1 (en) 2004-12-13

Similar Documents

Publication Publication Date Title
US6632875B2 (en) Polyurethane-forming composition with adjustable mix viscosity, geotextile composites prepared therefrom and a process for producing such composites
US6669407B2 (en) Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof
US6602025B2 (en) Process for lining canals, ditches and pipes with a non-sagging polyurethane/geofabric composite
US20030206775A1 (en) Polyurethane/geotextile composite liner for canals and ditches based on liquefied monomeric MDI-derivatives
US20020168531A1 (en) Two-ply polyurethane/geotextile composite and process for preparing the same
US6582771B1 (en) Method for producing a polyurethane/geofabric composite
US20020168907A1 (en) Polyurethane/geotextile composite and a process related thereto for the production thereof
AU2002250289A1 (en) Polyurethane geotextile composite liner with improved water resistance and a process for the production thereof
AU2002242331A1 (en) Improved polyurethane/geotextile composite and a process related thereto for the production thereof
AU2002242332A1 (en) Two-ply polyurethane/geotextile composite and process for preparing the same
AU2002248598A1 (en) Polyurethane-forming composition with adjustable mix viscosity, geotextile composites prepared therefrom and a process for producing such composites
AU2002244278A1 (en) Process for lining canals, ditches and pipes with a non-sagging polyurethane/geofabric composite

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG UZ VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2002719191

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 813/MUMNP/2003

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2002250289

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2440881

Country of ref document: CA

Ref document number: PA/a/2003/008233

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 2003/07149

Country of ref document: ZA

Ref document number: 200307149

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 028066030

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 2002719191

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: JP

WWW Wipo information: withdrawn in national office

Ref document number: JP

WWW Wipo information: withdrawn in national office

Ref document number: 2002719191

Country of ref document: EP